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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014615

Secondary Accession Numbers

HMDB14615

Metabolite Identification

Common Name

Fluoxetine

Description

Fluoxetine hydrochloride is the first agent of the class of antidepressants known as selective serotonin-reuptake inhibitors (SSRIs). Despite distinct structural differences between compounds in this class, SSRIs possess similar pharmacological activity. As with other antidepressant agents, several weeks of therapy may be required before a clinical effect is seen. SSRIs are potent inhibitors of neuronal serotonin reuptake. They have little to no effect on norepinephrine or dopamine reuptake and do not antagonize α- or β-adrenergic, dopamine D₂ or histamine H₁ receptors. During acute use, SSRIs block serotonin reuptake and increase serotonin stimulation of somatodendritic 5-HT_1A and terminal autoreceptors. Chronic use leads to desensitization of somatodendritic 5-HT_1A and terminal autoreceptors. The overall clinical effect of increased mood and decreased anxiety is thought to be due to adaptive changes in neuronal function that lead to enhanced serotonergic neurotransmission. Side effects include dry mouth, nausea, dizziness, drowsiness, sexual dysfunction, and headache. Side effects generally occur within the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants. Fluoxetine may be used to treat major depressive disorder (MDD), moderate to severe bulimia nervosa, obsessive-compulsive disorder (OCD), premenstrual dysphoric disorder (PMDD), panic disorder with or without agoraphobia, and, in combination with olanzapine, for treatment-resistant or bipolar I depression. Fluoxetine is the most anorexic and stimulating SSRI.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0243729
     RDKit          3D
(S)-Fluoxetine
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.1456   -3.0202    1.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7320   -3.0834    0.0770 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6530   -2.1762   -0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1256   -0.7393   -0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9573    0.1574   -0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0710   -0.0473    0.5010 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055   -0.2174    0.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0168   -0.1504   -0.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3728   -0.3310   -1.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1359   -0.5796    0.1120 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6140   -0.7773   -0.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0020   -0.0725   -1.1582 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.2956   -0.4206    1.1011 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8397   -2.1521   -0.2223 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5324   -0.6495    1.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -0.4687    1.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3748    1.6058   -0.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0112    2.0579   -1.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3654    3.3915   -1.6512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0794    4.2208   -0.5980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460    3.7453    0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0756    2.4104    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2608   -3.1980    2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9222   -3.8166    1.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6408   -2.0579    1.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958   -3.0238   -0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7937   -2.3237    0.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517   -2.4043   -1.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9321   -0.5502   -0.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5313   -0.5308    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6452   -0.0689   -1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4316    0.0511   -1.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8672   -0.2723   -1.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1770   -0.8511    2.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7142   -0.5362    2.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2396    1.3919   -2.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8705    3.8332   -2.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3380    5.2703   -0.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1848    4.3533    1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5698    2.0302    1.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 10 15  1  0
 15 16  2  0
  5 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 16  7  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  8 32  1  0
  9 33  1  0
 15 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
M  END

472
  Mrv0541 02231214422D          

 22 23  0  0  1  0            999 V2000
    4.3974    2.6813    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475    2.6813    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.5063    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 22  1  0  0  0  0
  2 22  1  0  0  0  0
  3 22  1  0  0  0  0
  4  6  1  0  0  0  0
  4 12  1  0  0  0  0
  5  9  1  0  0  0  0
  5 19  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  2  0  0  0  0
 12 15  2  0  0  0  0
 12 16  1  0  0  0  0
 13 18  2  0  0  0  0
 14 18  1  0  0  0  0
 15 20  1  0  0  0  0
 16 21  2  0  0  0  0
 17 20  2  0  0  0  0
 17 21  1  0  0  0  0
 17 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014615

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H18F3NO/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18,19)20/h2-10,16,21H,11-12H2,1H3

> <INCHI_KEY>
RTHCYVBBDHJXIQ-UHFFFAOYSA-N

> <FORMULA>
C17H18F3NO

> <MOLECULAR_WEIGHT>
309.3261

> <EXACT_MASS>
309.134048818

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
30.326618157922514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl})amine

> <ALOGPS_LOGP>
4.09

> <JCHEM_LOGP>
4.1732195433333334

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.80313944120745

> <JCHEM_POLAR_SURFACE_AREA>
21.259999999999998

> <JCHEM_REFRACTIVITY>
80.36750000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fluoxetine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0243729
     RDKit          3D
(S)-Fluoxetine
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.1456   -3.0202    1.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7320   -3.0834    0.0770 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6530   -2.1762   -0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1256   -0.7393   -0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9573    0.1574   -0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0710   -0.0473    0.5010 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055   -0.2174    0.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0168   -0.1504   -0.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3728   -0.3310   -1.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1359   -0.5796    0.1120 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6140   -0.7773   -0.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0020   -0.0725   -1.1582 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.2956   -0.4206    1.1011 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8397   -2.1521   -0.2223 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5324   -0.6495    1.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -0.4687    1.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3748    1.6058   -0.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0112    2.0579   -1.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3654    3.3915   -1.6512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0794    4.2208   -0.5980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460    3.7453    0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0756    2.4104    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2608   -3.1980    2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9222   -3.8166    1.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6408   -2.0579    1.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958   -3.0238   -0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7937   -2.3237    0.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517   -2.4043   -1.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9321   -0.5502   -0.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5313   -0.5308    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6452   -0.0689   -1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4316    0.0511   -1.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8672   -0.2723   -1.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1770   -0.8511    2.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7142   -0.5362    2.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2396    1.3919   -2.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8705    3.8332   -2.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3380    5.2703   -0.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1848    4.3533    1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5698    2.0302    1.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 10 15  1  0
 15 16  2  0
  5 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 16  7  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  8 32  1  0
  9 33  1  0
 15 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 472                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       8.208   5.005   0.000  0.00  0.00           F+0
HETATM    2  F   UNK     0      11.289   5.005   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       9.748   6.545   0.000  0.00  0.00           F+0
HETATM    4  O   UNK     0       9.748  -1.155   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       4.414  -1.155   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       8.415  -1.925   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081  -1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415  -3.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748  -1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748  -4.235   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -4.235   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.748   0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748  -5.775   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -5.775   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.082   1.155   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415   1.155   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748   3.465   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415  -6.545   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.080  -1.925   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.082   2.695   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.415   2.695   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.748   5.005   0.000  0.00  0.00           C+0
CONECT    1   22                                                            
CONECT    2   22                                                            
CONECT    3   22                                                            
CONECT    4    6   12                                                       
CONECT    5    9   19                                                       
CONECT    6    4    7    8                                                  
CONECT    7    6    9                                                       
CONECT    8    6   10   11                                                  
CONECT    9    5    7                                                       
CONECT   10    8   13                                                       
CONECT   11    8   14                                                       
CONECT   12    4   15   16                                                  
CONECT   13   10   18                                                       
CONECT   14   11   18                                                       
CONECT   15   12   20                                                       
CONECT   16   12   21                                                       
CONECT   17   20   21   22                                                  
CONECT   18   13   14                                                       
CONECT   19    5                                                            
CONECT   20   15   17                                                       
CONECT   21   16   17                                                       
CONECT   22    1    2    3   17                                             
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0243729
HETATM    1  C1  UNL     1      -3.146  -3.020   1.435  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.732  -3.083   0.077  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.653  -2.176  -0.176  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.126  -0.739  -0.091  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.957   0.157  -0.392  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.071  -0.047   0.501  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.406  -0.217   0.319  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.017  -0.150  -0.914  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.373  -0.331  -1.008  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.136  -0.580   0.112  1.00  0.00           C  
HETATM   11  C9  UNL     1       5.614  -0.777  -0.043  1.00  0.00           C  
HETATM   12  F1  UNL     1       6.002  -0.072  -1.158  1.00  0.00           F  
HETATM   13  F2  UNL     1       6.296  -0.421   1.101  1.00  0.00           F  
HETATM   14  F3  UNL     1       5.840  -2.152  -0.222  1.00  0.00           F  
HETATM   15  C10 UNL     1       3.532  -0.650   1.352  1.00  0.00           C  
HETATM   16  C11 UNL     1       2.167  -0.469   1.453  1.00  0.00           C  
HETATM   17  C12 UNL     1      -1.375   1.606  -0.458  1.00  0.00           C  
HETATM   18  C13 UNL     1      -2.011   2.058  -1.590  1.00  0.00           C  
HETATM   19  C14 UNL     1      -2.365   3.391  -1.651  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.079   4.221  -0.598  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.446   3.745   0.518  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.076   2.410   0.609  1.00  0.00           C  
HETATM   23  H1  UNL     1      -2.261  -3.198   2.095  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.922  -3.817   1.598  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.641  -2.058   1.631  1.00  0.00           H  
HETATM   26  H4  UNL     1      -3.496  -3.024  -0.595  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.794  -2.324   0.517  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.252  -2.404  -1.206  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.932  -0.550  -0.843  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.531  -0.531   0.920  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.645  -0.069  -1.464  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.432   0.051  -1.810  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.867  -0.272  -1.985  1.00  0.00           H  
HETATM   34  H12 UNL     1       4.177  -0.851   2.202  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.714  -0.536   2.432  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.240   1.392  -2.438  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.871   3.833  -2.503  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.338   5.270  -0.597  1.00  0.00           H  
HETATM   39  H17 UNL     1      -1.185   4.353   1.390  1.00  0.00           H  
HETATM   40  H18 UNL     1      -0.570   2.030   1.482  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   17   31
CONECT    6    7
CONECT    7    8    8   16
CONECT    8    9   32
CONECT    9   10   10   33
CONECT   10   11   15
CONECT   11   12   13   14
CONECT   15   16   16   34
CONECT   16   35
CONECT   17   18   18   22
CONECT   18   19   36
CONECT   19   20   20   37
CONECT   20   21   38
CONECT   21   22   22   39
CONECT   22   40
END

HMDB0243729
     RDKit          3D
(S)-Fluoxetine
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.1456   -3.0202    1.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7320   -3.0834    0.0770 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6530   -2.1762   -0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1256   -0.7393   -0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9573    0.1574   -0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0710   -0.0473    0.5010 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055   -0.2174    0.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0168   -0.1504   -0.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3728   -0.3310   -1.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1359   -0.5796    0.1120 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6140   -0.7773   -0.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0020   -0.0725   -1.1582 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.2956   -0.4206    1.1011 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8397   -2.1521   -0.2223 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5324   -0.6495    1.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -0.4687    1.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3748    1.6058   -0.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0112    2.0579   -1.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3654    3.3915   -1.6512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0794    4.2208   -0.5980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460    3.7453    0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0756    2.4104    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2608   -3.1980    2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9222   -3.8166    1.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6408   -2.0579    1.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958   -3.0238   -0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7937   -2.3237    0.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517   -2.4043   -1.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9321   -0.5502   -0.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5313   -0.5308    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6452   -0.0689   -1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4316    0.0511   -1.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8672   -0.2723   -1.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1770   -0.8511    2.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7142   -0.5362    2.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2396    1.3919   -2.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8705    3.8332   -2.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3380    5.2703   -0.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1848    4.3533    1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5698    2.0302    1.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 10 15  1  0
 15 16  2  0
  5 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 16  7  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  8 32  1  0
  9 33  1  0
 15 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Sarafem	ChEMBL, HMDB, MeSH
Symbyax	ChEMBL, HMDB
Prozac	ChEMBL, HMDB, MeSH
Fluoxetine hydrochloride	MeSH, HMDB
N-Methyl-gamma-(4-(trifluoromethyl)phenoxy)benzenepropanamine	MeSH, HMDB
Fluoxetin	MeSH, HMDB

Chemical Formula

C₁₇H₁₈F₃NO

Average Molecular Weight

309.3261

Monoisotopic Molecular Weight

309.134048818

IUPAC Name

methyl({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl})amine

Traditional Name

fluoxetine

CAS Registry Number

54910-89-3

SMILES

CNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H18F3NO/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18,19)20/h2-10,16,21H,11-12H2,1H3

InChI Key

RTHCYVBBDHJXIQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Trifluoromethylbenzenes

Direct Parent

Trifluoromethylbenzenes

Alternative Parents

Substituents

Trifluoromethylbenzene
Phenoxy compound
Phenol ether
Alkyl aryl ether
Aralkylamine
Secondary aliphatic amine
Ether
Secondary amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Alkyl fluoride
Organic nitrogen compound
Amine
Alkyl halide
Organopnictogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:86990 )
secondary amino compound (CHEBI:86990 )
(trifluoromethyl)benzenes (CHEBI:86990 )

Ontology

Not Available

Non-excretory biofluid

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	179 - 182 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0017 g/L	Not Available
LogP	4.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	176.5	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0017 g/L	ALOGPS
logP	4.09	ALOGPS
logP	4.17	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	9.8	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	21.26 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	80.37 m³·mol⁻¹	ChemAxon
Polarizability	30.33 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	173.3	30932474
DeepCCS	[M-H]-	170.942	30932474
DeepCCS	[M-2H]-	203.828	30932474
DeepCCS	[M+Na]+	179.393	30932474
AllCCS	[M+H]+	171.6	32859911
AllCCS	[M+H-H2O]+	168.2	32859911
AllCCS	[M+NH4]+	174.7	32859911
AllCCS	[M+Na]+	175.6	32859911
AllCCS	[M-H]-	172.4	32859911
AllCCS	[M+Na-2H]-	172.0	32859911
AllCCS	[M+HCOO]-	171.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fluoxetine	CNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1	2308.6	Standard polar	33892256
Fluoxetine	CNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1	1900.2	Standard non polar	33892256
Fluoxetine	CNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1	1885.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fluoxetine,1TMS,isomer #1	CN(CCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1)[Si](C)(C)C	2111.1	Semi standard non polar	33892256
Fluoxetine,1TMS,isomer #1	CN(CCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1)[Si](C)(C)C	2046.4	Standard non polar	33892256
Fluoxetine,1TMS,isomer #1	CN(CCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1)[Si](C)(C)C	2338.0	Standard polar	33892256
Fluoxetine,1TBDMS,isomer #1	CN(CCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2315.2	Semi standard non polar	33892256
Fluoxetine,1TBDMS,isomer #1	CN(CCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2235.5	Standard non polar	33892256
Fluoxetine,1TBDMS,isomer #1	CN(CCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2453.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Fluoxetine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9530000000-45c870b2463186b9230c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluoxetine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluoxetine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluoxetine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluoxetine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9200000000-dcf68dbfd090c7fdfe11	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluoxetine LC-ESI-qTof , Positive-QTOF	splash10-01t9-0592000000-92a48c620c961fdb430f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluoxetine LC-ESI-QTOF , positive-QTOF	splash10-03di-0009000000-ed61090013f0dc5f5c5a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluoxetine LC-ESI-QTOF , positive-QTOF	splash10-014i-0190000000-e9bcd2accdf5b7e40a88	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluoxetine LC-ESI-QTOF , positive-QTOF	splash10-014i-0590000000-04b1d4265cb156217f40	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluoxetine LC-ESI-QTOF , positive-QTOF	splash10-014i-0790000000-5c42b9a9a2cd0c4114aa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluoxetine LC-ESI-QTOF , positive-QTOF	splash10-0gb9-0960000000-88822d2fb3e7c0cdc0b3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOF	splash10-0002-0900000000-6b560941c92823b7901c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOF	splash10-03di-0109000000-1531c1e1630dcb42b497	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOF	splash10-0006-9000000000-53199cfe3b343ae81afd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOF	splash10-03di-0109000000-0e790a7e6032e51bfeb3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOF	splash10-00kf-9800000000-64d39c4a4fcc7f8b6f47	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOF	splash10-00kf-9700000000-e516356ce3eca65bece8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOF	splash10-0002-0900000000-6b560941c92823b7901c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOF	splash10-0zgi-1390000000-84c6bc70aefcd3758f31	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOF	splash10-0f7o-6940000000-a424e26ecc7465229968	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOF	splash10-0a4m-0390000000-9b7253cd5718aa434e46	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluoxetine LC-ESI-ITFT , positive-QTOF	splash10-0a4m-0290000000-d88f8004205c7223aa9f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluoxetine , positive-QTOF	splash10-01t9-0592000000-92a48c620c961fdb430f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluoxetine LC-ESI-QFT , positive-QTOF	splash10-03di-0409000000-03f5678c6178e634f254	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoxetine 10V, Positive-QTOF	splash10-03fr-1179000000-9f0773309b13bac8c304	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoxetine 20V, Positive-QTOF	splash10-0h03-5292000000-1e7d8430611731d4e4a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoxetine 40V, Positive-QTOF	splash10-0006-9830000000-b2a37ff34ba2d3974989	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoxetine 10V, Negative-QTOF	splash10-0a4i-1009000000-113c9621ae90d769ee33	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoxetine 20V, Negative-QTOF	splash10-0a4i-3469000000-4480faded690242a155c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoxetine 40V, Negative-QTOF	splash10-03di-2910000000-2c7cf659d217661ff897	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Fluoxetine Action Pathway		Not Available
Fluoxetine Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00472	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00472	21059682	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3269

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3386

PDB ID

Not Available

ChEBI ID

86990

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Wong DT, Horng JS, Bymaster FP, Hauser KL, Molloy BB: A selective inhibitor of serotonin uptake: Lilly 110140, 3-(p-trifluoromethylphenoxy)-N-methyl-3-phenylpropylamine. Life Sci. 1974 Aug 1;15(3):471-9. [PubMed:4549929 ]
Wong DT, Bymaster FP, Engleman EA: Prozac (fluoxetine, Lilly 110140), the first selective serotonin uptake inhibitor and an antidepressant drug: twenty years since its first publication. Life Sci. 1995;57(5):411-41. [PubMed:7623609 ]
Carlsson A, Wong DT: Correction: a note on the discovery of selective serotonin reuptake inhibitors. Life Sci. 1997;61(12):1203. [PubMed:9315511 ]
Caley CF: Extrapyramidal reactions and the selective serotonin-reuptake inhibitors. Ann Pharmacother. 1997 Dec;31(12):1481-9. [PubMed:9416386 ]
Gerber PE, Lynd LD: Selective serotonin-reuptake inhibitor-induced movement disorders. Ann Pharmacother. 1998 Jun;32(6):692-8. [PubMed:9640489 ]

Showing metabocard for Fluoxetine (HMDB0014615)

MOL for HMDB0014615 (Fluoxetine)

3D MOL for HMDB0014615 (Fluoxetine)

3D SDF for HMDB0014615 (Fluoxetine)

3D-SDF for HMDB0014615 (Fluoxetine)

PDB for HMDB0014615 (Fluoxetine)

3D PDB for HMDB0014615 (Fluoxetine)

SMILES for HMDB0014615 (Fluoxetine)

INCHI for HMDB0014615 (Fluoxetine)

Structure for HMDB0014615 (Fluoxetine)

3D Structure for HMDB0014615 (Fluoxetine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra